Director of Technical Services

Job Description We are seeking a Director of Technical Operations to work on service technology in Small Business Services. This is a high-impact director-level position that combines technical leadership, project orchestration, and cross-functional coordination to drive business outcomes through innovation and client obsession.

The ideal candidate will bring 8+ years of experience in product management or similar fields, with proven expertise in both managing complex internal projects and collaborating with engineering teams to deliver customer-facing capabilities.

Key Responsibilities Technical Project & Portfolio Management
· Manage the intake and prioritization of data science, tools, and feature requests from internal stakeholders
· Define scope, refine requirements, and establish success criteria for technical projects
· Partner with product owners to deliver
· Provide thoughtful analysis that tells us what outcomes our work is providing, and where we need to double down
· Maintain visibility into the portfolio of ongoing technical projects and ensure strategic alignment

Cross-Functional Product Coordination
· Partner with the Service Technology Engineering team to translate business needs into technical solutions
· Act as a product strategist (not a product owner managing backlogs, but a strategic advisor on technical direction)
· Collaborate with business stakeholders, engineering, design, and UX research teams to clarify priorities and unblock work
· Work positively and effectively with internal customers including client service associates, executives, and frontline managers

Stakeholder Management & Communication
· Serve as a bridge between technical teams, business leaders, and users
· Gather insights from client data, analytics, and direct user feedback to inform service technology decisions
· Communicate technical constraints and tradeoffs to non-technical stakeholders
· Maintain a data-driven approach to prioritization and decision-making

Strategic Leadership
· Use analytics and customer insights to understand what he business actually needs
· Develop evidence-based opinions and validate them through research
· Navigate ambiguity and make progress without waiting for perfect information
· Keep teams energized and moving forward with optimistic, collaborative leadership

What We're Looking For Core Competencies (Required)
· Bachelor's degree in a technical, analytical, or business-related field (or equivalent experience)
· 8+ years of proven experience in product management, technical operations, or related roles
· Full SDLC expertise - demonstrated success from discovery through launch and post-launch analysis
· Technical acumen - Ability to engage deeply with engineers on technical decisions, architecture, and system design
· Data fluency - Comfortable with analytics tools, can pull reports, interpret data, and act on insights independently
· Clear communicator - Can write business cases, run productive meetings, and explain technical concepts to diverse audiences
· Comfortable with ambiguity - Makes progress without complete information and course-corrects quickly
· Naturally collaborative - Works well with engineering, design, business teams; shares perspectives and commits fully once direction is set
· Client obsessed - Stays close to real users through calls, session recordings, support tickets, and ongoing research

Job Requirements

Preferred Qualifications
· Regulated industry experience - Background in payroll, HR, tax, fintech, healthcare, or similar domains where compliance and accuracy are critical
· AI/Automation expertise - Hands-on experience integrating GenAI or LLM tooling into workflows; understands capabilities and limitations
· Technical background - Some hands-on experience with…